Dapivirine (BioDeep_00000858724)
代谢物信息卡片
Dapivirine (TMC120)
化学式: C20H19N5 (329.164)
中文名称: Dapivirine
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1=CC(=C(C(=C1)C)NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C
InChI: InChI=1S/C20H19N5/c1-13-10-14(2)19(15(3)11-13)24-18-8-9-22-20(25-18)23-17-6-4-16(12-21)5-7-17/h4-11H,1-3H3,(H2,22,23,24,25)
描述信息
G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids
C471 - Enzyme Inhibitor > C1589 - Reverse Transcriptase Inhibitor > C97453 - Non-nucleoside Reverse Transcriptase Inhibitor
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents
C254 - Anti-Infective Agent > C281 - Antiviral Agent
同义名列表
2 个代谢物同义名
数据库引用编号
5 个数据库交叉引用编号
- KEGGdrug: D11246
- PubChem: 214347
- DrugBank: DB08639
- ChEMBL: CHEMBL70663
- CAS: 244767-67-7
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
- Ross D Cranston, Elizabeth Brown, José Bauermeister, Eileen F Dunne, Craig Hoesley, Ken Ho, Sherri Johnson, Jonathan Lucas, Clara Dominguez-Islas, Holly Gundacker, Melissa Peda, Cindy E Jacobson, Lindsay Kramzer, Devika Singh, Charlene S Dezzutti, Ratiya Pamela Kunjara Na Ayudhya, Rhonda M Brand, Lin Wang, Mark A Marzinke, Jeanna Piper, Bríd Devlin, Jeremy Nuttall, Ian McGowan, Craig W Hendrix. A Randomized, Double Blind, Placebo-Controlled, Phase 1 Safety, and Pharmacokinetic Study of Dapivirine Gel (0.05\%) Administered Rectally to HIV-1 Seronegative Adults (MTN-026).
AIDS research and human retroviruses.
2022 04; 38(4):257-268. doi:
10.1089/aid.2021.0071. [PMID: 34498980] - Urvi M Parikh, Kerri J Penrose, Amy L Heaps, Elias K Halvas, B Jay Goetz, Kelley C Gordon, Russell Hardesty, Rahil Sethi, William Schwarzmann, Daniel W Szydlo, Marla J Husnik, Uma Chandran, Thesla Palanee-Phillips, Jared M Baeten, John W Mellors. HIV-1 drug resistance among individuals who seroconverted in the ASPIRE dapivirine ring trial.
Journal of the International AIDS Society.
2021 11; 24(11):e25833. doi:
10.1002/jia2.25833. [PMID: 34762770] - Marla J Husnik, Elizabeth R Brown, Sufia S Dadabhai, Zakir Gaffoor, Nitesha Jeenarain, Flavia Matovu Kiweewa, Edward Livant, Leila E Mansoor, Brenda Gati Mirembe, Thesla Palanee-Phillips, Devika Singh, Samantha Siva, Lydia Soto-Torres, Ariane van der Straten, Jared M Baeten. Correlates of Adherence to the Dapivirine Vaginal Ring for HIV-1 Prevention.
AIDS and behavior.
2021 Sep; 25(9):2801-2814. doi:
10.1007/s10461-021-03231-x. [PMID: 34117592] - Albert Y Liu, Clara Dominguez Islas, Holly Gundacker, Blazej Neradilek, Craig Hoesley, Ariane van der Straten, Craig W Hendrix, May Beamer, Cindy E Jacobson, Tara McClure, Tanya Harrell, Katherine Bunge, Brid Devlin, Jeremy Nuttall, Patrick Spence, John Steytler, Jeanna M Piper, Mark A Marzinke. Phase 1 pharmacokinetics and safety study of extended duration dapivirine vaginal rings in the United States.
Journal of the International AIDS Society.
2021 06; 24(6):e25747. doi:
10.1002/jia2.25747. [PMID: 34118115] - Farnaz Minooei, Joel R Fried, Joshua L Fuqua, Kenneth E Palmer, Jill M Steinbach-Rankins. In vitro Study on Synergistic Interactions Between Free and Encapsulated Q-Griffithsin and Antiretrovirals Against HIV-1 Infection.
International journal of nanomedicine.
2021; 16(?):1189-1206. doi:
10.2147/ijn.s287310. [PMID: 33623382] - Madhuri Manohar, Mark A Marzinke. Validation and implementation of an ultrasensitive liquid chromatographic-tandem mass spectrometric (LC-MS/MS) assay for dapivirine quantitation in breast milk.
Clinical biochemistry.
2020 Aug; 82(?):66-72. doi:
10.1016/j.clinbiochem.2019.12.005. [PMID: 31843664] - Katherine E Bunge, Lisa Levy, Daniel W Szydlo, Jingyang Zhang, Aditya H Gaur, Daniel Reirden, Kenneth H Mayer, Donna Futterman, Craig Hoesley, Sharon L Hillier, Mark A Marzinke, Craig W Hendrix, Pamina M Gorbach, Craig M Wilson, Lydia Soto-Torres, Bill Kapogiannis, Annalene Nel, Kathleen E Squires. Brief Report: Phase IIa Safety Study of a Vaginal Ring Containing Dapivirine in Adolescent Young Women.
Journal of acquired immune deficiency syndromes (1999).
2020 02; 83(2):135-139. doi:
10.1097/qai.0000000000002244. [PMID: 31929401] - Sharon A Riddler, Jennifer E Balkus, Urvi M Parikh, John W Mellors, Carolyne Akello, Sufia Dadabhai, Felix Mhlanga, Gita Ramjee, Ashley J Mayo, Edward Livant, Amy L Heaps, Colin O'Rourke, Jared M Baeten. Clinical and Virologic Outcomes Following Initiation of Antiretroviral Therapy Among Seroconverters in the Microbicide Trials Network-020 Phase III Trial of the Dapivirine Vaginal Ring.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.
2019 07; 69(3):523-529. doi:
10.1093/cid/ciy909. [PMID: 30346511] - Ariane van der Straten, Erica N Browne, Mary Kate Shapley-Quinn, Elizabeth R Brown, Krishnaveni Reddy, Rachel Scheckter, Lydia Soto-Torres, Thesla Palanee-Phillips, Jared M Baeten, Barbara Mensch. First Impressions Matter: How Initial Worries Influence Adherence to the Dapivirine Vaginal Ring.
Journal of acquired immune deficiency syndromes (1999).
2019 07; 81(3):304-310. doi:
10.1097/qai.0000000000002028. [PMID: 30844995] - Beatrice A Chen, Jingyang Zhang, Holly M Gundacker, Craig W Hendrix, Craig J Hoesley, Robert A Salata, Charlene S Dezzutti, Ariane van der Straten, Wayne B Hall, Cindy E Jacobson, Sherri Johnson, Ian McGowan, Annalene M Nel, Lydia Soto-Torres, Mark A Marzinke. Phase 2a Safety, Pharmacokinetics, and Acceptability of Dapivirine Vaginal Rings in US Postmenopausal Women.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.
2019 03; 68(7):1144-1151. doi:
10.1093/cid/ciy654. [PMID: 30289485] - Lisa M Noguchi, Craig Hoesley, Cliff Kelly, Rachel Scheckter, Katherine Bunge, Annalene Nel, Mark A Marzinke, Craig W Hendrix, Charlene S Dezzutti, Sharon L Hillier, Debra L Bogen, Jeanna M Piper, Richard H Beigi. Pharmacokinetics of Dapivirine Transfer into Blood Plasma, Breast Milk, and Cervicovaginal Fluid of Lactating Women Using the Dapivirine Vaginal Ring.
Antimicrobial agents and chemotherapy.
2019 03; 63(3):. doi:
10.1128/aac.01930-18. [PMID: 30602513] - Barbara S Mensch, Barbra A Richardson, Marla Husnik, Elizabeth R Brown, Flavia Matovu Kiweewa, Ashley J Mayo, Jared M Baeten, Thesla Palanee-Phillips, Ariane van der Straten. Vaginal Ring Use in a Phase 3 Microbicide Trial: A Comparison of Objective Measures and Self-reports of Non-adherence in ASPIRE.
AIDS and behavior.
2019 Feb; 23(2):504-512. doi:
10.1007/s10461-018-2261-8. [PMID: 30218318] - Thesla Palanee-Phillips, Sarah T Roberts, Krishnaveni Reddy, Vaneshree Govender, Logashvari Naidoo, Samantha Siva, Zakir Gafoor, Arendevi Pather, Flavia Matovu, Kudzai Hlahla, Bonus Makanani, Gonasagrie Nair, Katie Schwartz, Kristine Torjesen, Elizabeth Brown, Lydia Soto-Torres, Jared Baeten, Elizabeth T Montgomery. Impact of Partner-Related Social Harms on Women's Adherence to the Dapivirine Vaginal Ring During a Phase III Trial.
Journal of acquired immune deficiency syndromes (1999).
2018 12; 79(5):580-589. doi:
10.1097/qai.0000000000001866. [PMID: 30239426] - Bonus Makanani, Jennifer E Balkus, Yuqing Jiao, Lisa M Noguchi, Thesla Palanee-Phillips, Yamikani Mbilizi, Jothi Moodley, Kenneth Kintu, Krishnaveni Reddy, Samuel Kabwigu, Nitesha Jeenariain, Ishana Harkoo, Nyaradzo Mgodi, Jeanna Piper, Helen Rees, Rachel Scheckter, Richard Beigi, Jared M Baeten. Pregnancy and Infant Outcomes Among Women Using the Dapivirine Vaginal Ring in Early Pregnancy.
Journal of acquired immune deficiency syndromes (1999).
2018 12; 79(5):566-572. doi:
10.1097/qai.0000000000001861. [PMID: 30383589] - Katherine Kay, Dhaval K Shah, Lisa Rohan, Robert Bies. Physiologically-based pharmacokinetic model of vaginally administered dapivirine ring and film formulations.
British journal of clinical pharmacology.
2018 09; 84(9):1950-1969. doi:
10.1111/bcp.13625. [PMID: 29714824] - Elizabeth T Montgomery, Jonathan Stadler, Sarita Naidoo, Ariana W K Katz, Nicole Laborde, Morgan Garcia, Krishnaveni Reddy, Leila E Mansoor, Juliane Etima, Chifundo Zimba, Miria Chitukuta, Lydia Soto-Torres. Reasons for nonadherence to the dapivirine vaginal ring: narrative explanations of objective drug-level results.
AIDS (London, England).
2018 07; 32(11):1517-1525. doi:
10.1097/qad.0000000000001868. [PMID: 29957723] - Marla J Husnik, Elizabeth R Brown, Mark Marzinke, Edward Livant, Thesla Palanee-Phillips, Craig W Hendrix, Flavia Matovu Kiweewa, Gonasagrie Nair, Lydia E Soto-Torres, Katie Schwartz, Sharon L Hillier, Jared M Baeten. Implementation of a Novel Adherence Monitoring Strategy in a Phase III, Blinded, Placebo-Controlled, HIV-1 Prevention Clinical Trial.
Journal of acquired immune deficiency syndromes (1999).
2017 11; 76(3):330-337. doi:
10.1097/qai.0000000000001503. [PMID: 28746164] - Jennifer E Balkus, Thesla Palanee-Phillips, Krishnaveni Reddy, Samantha Siva, Ishana Harkoo, Clemensia Nakabiito, Kenneth Kintu, Gonasangrie Nair, Catherine Chappell, Flavia Matovu Kiweewa, Samuel Kabwigu, Logashvari Naidoo, Nitesha Jeenarain, Mark Marzinke, Lydia Soto-Torres, Elizabeth R Brown, Jared M Baeten. Brief Report: Dapivirine Vaginal Ring Use Does Not Diminish the Effectiveness of Hormonal Contraception.
Journal of acquired immune deficiency syndromes (1999).
2017 10; 76(2):e47-e51. doi:
10.1097/qai.0000000000001455. [PMID: 28542081] - Yanmei Hu, Jiantao Zhang, Rami Ghassan Musharrafieh, Chunlong Ma, Raymond Hau, Jun Wang. Discovery of dapivirine, a nonnucleoside HIV-1 reverse transcriptase inhibitor, as a broad-spectrum antiviral against both influenza A and B viruses.
Antiviral research.
2017 Sep; 145(?):103-113. doi:
10.1016/j.antiviral.2017.07.016. [PMID: 28778830] - Jennifer A Robinson, Mark A Marzinke, Rahul P Bakshi, Edward J Fuchs, Christine L Radebaugh, Wutyi Aung, Hans M L Spiegel, Jenell S Coleman, Lisa C Rohan, Craig W Hendrix. Comparison of Dapivirine Vaginal Gel and Film Formulation Pharmacokinetics and Pharmacodynamics (FAME 02B).
AIDS research and human retroviruses.
2017 04; 33(4):339-346. doi:
10.1089/aid.2016.0040. [PMID: 27809557] - Kerri J Penrose, Carole L Wallis, Chanson J Brumme, Kristen A Hamanishi, Kelley C Gordon, Raquel V Viana, P Richard Harrigan, John W Mellors, Urvi M Parikh. Frequent Cross-Resistance to Dapivirine in HIV-1 Subtype C-Infected Individuals after First-Line Antiretroviral Therapy Failure in South Africa.
Antimicrobial agents and chemotherapy.
2017 02; 61(2):. doi:
10.1128/aac.01805-16. [PMID: 27895013] - Michael E Halwes, Jill M Steinbach-Rankins, Hermann B Frieboes. Pharmacokinetic modeling of a gel-delivered dapivirine microbicide in humans.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2016 Oct; 93(?):410-8. doi:
10.1016/j.ejps.2016.08.037. [PMID: 27559026] - Charlene S Dezzutti, Nicola Richardson-Harman, Lisa C Rohan, Mark A Marzinke, Craig J Hoesley, Lori Panther, Sherri Johnson, Jeremy P Nuttall, Annalene Nel, Beatrice A Chen. Pharmacodynamic correlations using fresh and cryopreserved tissue following use of vaginal rings containing dapivirine and/or maraviroc in a randomized, placebo controlled trial.
Medicine.
2016 Jul; 95(28):e4174. doi:
10.1097/md.0000000000004174. [PMID: 27428211] - Katherine E Bunge, Charlene S Dezzutti, Lisa C Rohan, Craig W Hendrix, Mark A Marzinke, Nicola Richardson-Harman, Bernard J Moncla, Brid Devlin, Leslie A Meyn, Hans M L Spiegel, Sharon L Hillier. A Phase 1 Trial to Assess the Safety, Acceptability, Pharmacokinetics, and Pharmacodynamics of a Novel Dapivirine Vaginal Film.
Journal of acquired immune deficiency syndromes (1999).
2016 Apr; 71(5):498-505. doi:
10.1097/qai.0000000000000897. [PMID: 26565716] - Annalene Nel, Linda-Gail Bekker, Elizabeth Bukusi, Elizabeth Hellstrӧm, Philip Kotze, Cheryl Louw, Francis Martinson, Gileard Masenga, Elizabeth Montgomery, Nelisiwe Ndaba, Ariane van der Straten, Neliëtte van Niekerk, Cynthia Woodsong. Safety, Acceptability and Adherence of Dapivirine Vaginal Ring in a Microbicide Clinical Trial Conducted in Multiple Countries in Sub-Saharan Africa.
PloS one.
2016; 11(3):e0147743. doi:
10.1371/journal.pone.0147743. [PMID: 26963505] - Beatrice A Chen, Lori Panther, Mark A Marzinke, Craig W Hendrix, Craig J Hoesley, Ariane van der Straten, Marla J Husnik, Lydia Soto-Torres, Annalene Nel, Sherri Johnson, Nicola Richardson-Harman, Lorna K Rabe, Charlene S Dezzutti. Phase 1 Safety, Pharmacokinetics, and Pharmacodynamics of Dapivirine and Maraviroc Vaginal Rings: A Double-Blind Randomized Trial.
Journal of acquired immune deficiency syndromes (1999).
2015 Nov; 70(3):242-9. doi:
10.1097/qai.0000000000000702. [PMID: 26034880] - Jonathon D S Holt, David Cameron, Nicola Dias, Jeremy Holding, Alex Muntendam, Freddy Oostebring, Peter Dreier, Lisa Rohan, Jeremy Nuttall. The sheep as a model of preclinical safety and pharmacokinetic evaluations of candidate microbicides.
Antimicrobial agents and chemotherapy.
2015 Jul; 59(7):3761-70. doi:
10.1128/aac.04954-14. [PMID: 25845860] - Diarmaid J Murphy, Delphine Desjardins, Nathalie Dereuddre-Bosquet, Patricia Brochard, Ludivine Perrot, Alain Pruvost, Roger Le Grand, Ole Lagatie, Leen Vanhooren, Maxim Feyaerts, Jens van Roey, R Karl Malcolm. Pre-clinical development of a combination microbicide vaginal ring containing dapivirine and darunavir.
The Journal of antimicrobial chemotherapy.
2014 Sep; 69(9):2477-88. doi:
10.1093/jac/dku160. [PMID: 24862093] - Annalene Nel, Wouter Haazen, Jeremy Nuttall, Joseph Romano, Zeda Rosenberg, Neliëtte van Niekerk. A safety and pharmacokinetic trial assessing delivery of dapivirine from a vaginal ring in healthy women.
AIDS (London, England).
2014 Jun; 28(10):1479-87. doi:
10.1097/qad.0000000000000280. [PMID: 24901365] - Ross D Cranston, Craig Hoesley, Alex Carballo-Diéguez, Craig W Hendrix, Marla Husnik, Lisa Levy, Wayne Hall, Lydia Soto-Torres, Annalene M Nel. A randomized male tolerance study of dapivirine gel following multiple topical penile exposures (MTN 012/IPM 010).
AIDS research and human retroviruses.
2014 Feb; 30(2):184-9. doi:
10.1089/aid.2013.0170. [PMID: 24070431] - Lauren A Seserko, Joshua F Emory, Craig W Hendrix, Mark A Marzinke. The development and validation of an UHPLC-MS/MS method for the rapid quantification of the antiretroviral agent dapivirine in human plasma.
Bioanalysis.
2013 Nov; 5(22):2771-83. doi:
10.4155/bio.13.256. [PMID: 24256358] - B J Moncla, K Pryke, L C Rohan, H Yang. Testing of viscous anti-HIV microbicides using Lactobacillus.
Journal of microbiological methods.
2012 Feb; 88(2):292-6. doi:
10.1016/j.mimet.2011.12.013. [PMID: 22226641] - Annalene M Nel, Paul Coplan, Shanique C Smythe, Karen McCord, Mark Mitchnick, Paulina E Kaptur, Joseph Romano. Pharmacokinetic assessment of dapivirine vaginal microbicide gel in healthy, HIV-negative women.
AIDS research and human retroviruses.
2010 Nov; 26(11):1181-90. doi:
10.1089/aid.2009.0227. [PMID: 20854207] - Annalene M Nel, Shanique C Smythe, Sepideh Habibi, Paulina E Kaptur, Joseph W Romano. Pharmacokinetics of 2 dapivirine vaginal microbicide gels and their safety vs. Hydroxyethyl cellulose-based universal placebo gel.
Journal of acquired immune deficiency syndromes (1999).
2010 Oct; 55(2):161-9. doi:
10.1097/qai.0b013e3181e3293a. [PMID: 20574411] - Annalene Nel, Shanique Smythe, Katherine Young, Karl Malcolm, Clare McCoy, Zeda Rosenberg, Joseph Romano. Safety and pharmacokinetics of dapivirine delivery from matrix and reservoir intravaginal rings to HIV-negative women.
Journal of acquired immune deficiency syndromes (1999).
2009 Aug; 51(4):416-23. doi:
10.1097/qai.0b013e3181acb536. [PMID: 19623693] - Annalene M Nel, Paul Coplan, Janneke H van de Wijgert, Saidi H Kapiga, Claire von Mollendorf, Eveline Geubbels, Joseph Vyankandondera, Helen V Rees, Gileard Masenga, Ireen Kiwelu, Jocelyn Moyes, Shanique C Smythe. Safety, tolerability, and systemic absorption of dapivirine vaginal microbicide gel in healthy, HIV-negative women.
AIDS (London, England).
2009 Jul; 23(12):1531-8. doi:
10.1097/qad.0b013e32832c413d. [PMID: 19550287] - J Romano, B Variano, P Coplan, J Van Roey, K Douville, Z Rosenberg, M Temmerman, H Verstraelen, L Van Bortel, S Weyers, M Mitchnick. Safety and availability of dapivirine (TMC120) delivered from an intravaginal ring.
AIDS research and human retroviruses.
2009 May; 25(5):483-8. doi:
10.1089/aid.2008.0184. [PMID: 19388819] - Jeremy P Nuttall, Daryl C Thake, Mark G Lewis, John W Ferkany, Joseph W Romano, Mark A Mitchnick. Concentrations of dapivirine in the rhesus macaque and rabbit following once daily intravaginal administration of a gel formulation of [14C]dapivirine for 7 days.
Antimicrobial agents and chemotherapy.
2008 Mar; 52(3):909-14. doi:
10.1128/aac.00330-07. [PMID: 18086845] - Vicky A Jespers, Jens M Van Roey, Greet I Beets, Anne M Buvé. Dose-ranging phase 1 study of TMC120, a promising vaginal microbicide, in HIV-negative and HIV-positive female volunteers.
Journal of acquired immune deficiency syndromes (1999).
2007 Feb; 44(2):154-8. doi:
10.1097/qai.0b013e31802bb35f. [PMID: 17106275] - Koen Andries, Hilde Azijn, Theo Thielemans, Donald Ludovici, Michael Kukla, Jan Heeres, Paul Janssen, Bart De Corte, Johan Vingerhoets, Rudi Pauwels, Marie-Pierre de Béthune. TMC125, a novel next-generation nonnucleoside reverse transcriptase inhibitor active against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus type 1.
Antimicrobial agents and chemotherapy.
2004 Dec; 48(12):4680-6. doi:
10.1128/aac.48.12.4680-4686.2004. [PMID: 15561844] - Paul Lewi, Eddy Arnold, Koen Andries, Hilde Bohets, Herman Borghys, Arthur Clark, Frits Daeyaert, Kalyan Das, Marie-Pierre de Béthune, Marc de Jonge, Jan Heeres, Luc Koymans, Jos Leempoels, Jef Peeters, Philip Timmerman, Walter Van den Broeck, Frédéric Vanhoutte, Gerben Van't Klooster, Maarten Vinkers, Yulia Volovik, Paul A J Janssen. Correlations between factors determining the pharmacokinetics and antiviral activity of HIV-1 non-nucleoside reverse transcriptase inhibitors of the diaryltriazine and diarylpyrimidine classes of compounds.
Drugs in R&D.
2004; 5(5):245-57. doi:
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